Headrests are often disposed on a seatback of a vehicle seat and can be uncomfortable, particularly when the headrest is not adjustable to suit the needs of a particular vehicle occupant. For tired passengers, long trips can leave a vehicle occupant with aches and pains associated with sleeping with their head disposed at an awkward angle. Thus, a headrest assembly is desired that provides full lateral support for the upper body by providing a surround configuration akin to a travel pillow when deployed.